DE1300727B - Use of dinitroaniline derivatives as selective pre-emergence herbicides - Google Patents

Use of dinitroaniline derivatives as selective pre-emergence herbicides

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Publication number
DE1300727B
DE1300727B DEE21584A DEE0021584A DE1300727B DE 1300727 B DE1300727 B DE 1300727B DE E21584 A DEE21584 A DE E21584A DE E0021584 A DEE0021584 A DE E0021584A DE 1300727 B DE1300727 B DE 1300727B
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Prior art keywords
dinitroaniline
propyl
dinitro
grasses
emergence
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DEE21584A
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German (de)
Inventor
Soper Quentin Francis
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Eli Lilly and Co
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Eli Lilly and Co
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Publication of DE1300727B publication Critical patent/DE1300727B/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
    • C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18—Nitro compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Die Erfindung betrifft die Verwendung von Dinitroanilinderivaten der allgemeinen FormelThe invention relates to the use of dinitroaniline derivatives of the general formula

NO,NO,

worin R für eine n-Alkylgruppe mit 2 bis 4 Kohlenstoffatomen oder die Allylgruppe steht, R' eine n-Alkylgruppe mit 1 bis 4 Kohlenstoffatomen oder die Allylgruppe bedeutet und R" Wasserstoff oder ein Halogenatom, die Trifiuormethylgruppe oder eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen ist, oder R und R' zusammen mit dem Stickstoffatom, mit welchem sie verknüpft sind, einen Piperidino- oder Pyrrolidinorest bilden, wenn R" eine andere Bedeutung als Wasserstoff besitzt, als selektive Vorauflaufherbizide.wherein R is an n-alkyl group having 2 to 4 carbon atoms or the allyl group, R 'is an n-alkyl group having 1 to 4 carbon atoms or the allyl group and R "denotes hydrogen or a halogen atom, the trifluoromethyl group or is an alkyl group with 1 to 4 carbon atoms, or R and R 'together with the nitrogen atom, to which they are linked, form a piperidino or pyrrolidino radical when R "is a has a different meaning than hydrogen, as selective pre-emergence herbicides.

Die erfindungsgemäß verwendeten substituierten Dinitroanilin-Verbindungen sind entweder niedrig schmelzende, gelbe, kristalline Stoffe oder stark viskose, orangefarbene öle. Sie lassen sich herstellen durch Erhitzen eines gegebenenfalls substituierten 2,6-Dinitrochlorbenzols mit einem sekundären Amin in einem inerten Lösungsmittel. Zum Beispiel kann man N,N-Di-n-propyl-2,6-dinitroanilin herstellen durch · Umsetzen von 2,6-Dinitrochlorbenzol mit überschüssigem Di-n-propylamin in einem geeigneten Lösungsmittel, wie Benzol oder Toluol. Der in der Reaktion als Nebenprodukt gebildete Chlorwasserstoff wird vom überschüssigen Di-n-propylamin aufgenommen unter Bildung des entsprechenden Chlorhydrats. Bei Verwendung eines unpolaren organischen Lösungsmittels, wie Benzol, in welchem das Chlorhydrat unlöslich ist, kann man das Salz durch Filtration abtrennen und das gewünschte N,N - Di - η - propyl - 2,6 - dinitroanilin durch Eindampfen des Filtrats isolieren. Bei Verwendung eines polaren organischen Lösungsmittels, wie Äthanol, in welchem das Chlorhydrat löslich ist, dampft man das Reaktionsgemisch zur Trockene ein und behandelt den Rückstand mit einem Gemisch aus Wasser und Äther. Das Chlorhydrat löst sich im Wasser, das N,N-Di-n-propyl-2,6-dinitroanilin geht in den Äther über und wird durch Verdampfen des Äthers isoliert. Verbindungen mit einem Substituenten in der p-Stellung des Anilins, wie Ν,Ν-Di-n-propyl-4-chlor-2,6-dinitroanilin und N,N - Di - η - propyl-2,6-dinitro-p-toluidin, werden in ähnlicher Weise unter Verwendung von 2,6-Dinitro-l,4-dichlorbenzol bzw. 3,5-Dinitro-4-chlortoluoI an Stelle des 2,6-Dinitrochlorbenzols hergestellt.The substituted dinitroaniline compounds used in the present invention are either low melting, yellow, crystalline substances or highly viscous, orange-colored oils. They can be made by heating an optionally substituted 2,6-dinitrochlorobenzene with a secondary amine in an inert solvent. For example, one can make N, N-di-n-propyl-2,6-dinitroaniline by reacting 2,6-dinitrochlorobenzene with excess di-n-propylamine in a suitable Solvents such as benzene or toluene. The hydrogen chloride formed as a by-product in the reaction is taken up by the excess di-n-propylamine with formation of the corresponding Chlorohydrates. When using a non-polar organic solvent such as benzene in which the chlorohydrate is insoluble, the salt can be separated off by filtration and the desired Isolate N, N - di - η - propyl - 2,6 - dinitroaniline by evaporating the filtrate. When using a A polar organic solvent, such as ethanol, in which the hydrochloride is soluble, is evaporated the reaction mixture to dryness and treated the residue with a mixture of water and ether. The chlorohydrate dissolves in the water, the N, N-di-n-propyl-2,6-dinitroaniline goes into the Ether over and is isolated by evaporation of the ether. Compounds with a substituent in the p-position of aniline, such as Ν, Ν-di-n-propyl-4-chloro-2,6-dinitroaniline and N, N - di - η - propyl-2,6-dinitro-p-toluidine, are made in a similar manner using 2,6-dinitro-1,4-dichlorobenzene or 3,5-dinitro-4-chlorotoluene instead of 2,6-dinitrochlorobenzene manufactured.

Bestimmte physikalische Daten für Verbindungen, die gemäß der Erfindung als Herbizide geeignet sind, werden in Tabelle I wiedergegeben. Auch enthält die Tabelle Angaben über die bei der Herstellung dieser Verbindungen nach dem obigen Verfahren verwendeten Reaktionsmedien und Lösungsmittel zur Umkristallisation.Certain physical data for compounds useful as herbicides according to the invention are given in Table I. The table also contains information about the production process of these compounds used in the above process reaction media and solvents for Recrystallization.

Tabelle I
Beispiele für Verbindungen, die zur Verwendung als Herbizide geeignet sindTable I.
Examples of compounds suitable for use as herbicides

Verbindunglink ReaktionsmediumReaction medium Lösungsmittel
zur Umkristaliisationsolvent
for recrystallization I Schmelzpunkt
CI melting point
C. N,N-Di-n-propyl-2,6-dinitroanilinN, N-di-n-propyl-2,6-dinitroaniline Benzolbenzene ÄthanolEthanol 50 bis 5250 to 52 N,N-Diäthyl-2,6-dinitroanilinN, N-diethyl-2,6-dinitroaniline Benzolbenzene ÄthanolEthanol 46 bis 4846 to 48 N,N-Di-n-butyl-2,6-dinitroanilinN, N-di-n-butyl-2,6-dinitroaniline Benzolbenzene ÄthanolEthanol unterhalb
Raumtemperaturbelow
Room temperature N,N-Di-allyl-2,6-dinitroanilinN, N-di-allyl-2,6-dinitroaniline Benzolbenzene ÄthanolEthanol 50,5 bis 5250.5 to 52 N,N-Di-n-propyl-4-chlor-
2,6-dinitroanilinN, N-di-n-propyl-4-chloro-
2,6-dinitroaniline XylolXylene ÄthanolEthanol 70 bis 7170 to 71 N,N-Di-n-propyl-2,6-dinitro-
p-toluidinN, N-di-n-propyl-2,6-dinitro-
p-toluidine ReaktionsteilnehmerRespondents HexanHexane 40 bis 4240 to 42 N-Äthyi-N-n-propyl-2,6-dinitroanilinN-Ethyi-N-n-propyl-2,6-dinitroaniline XylolXylene ÄthanolEthanol 38 bis 4038 to 40 N-n-Butyl-N-n-propyl-2,6-dinitroaniIinN-n-Butyl-N-n-propyl-2,6-dinitroaniIine ReaktionsteilnehmerRespondents HexanHexane unterhalb
Raumtemperaturbelow
Room temperature N.N-Diäthyl^-chior^o-dinitroanilinN.N-diethyl ^ -chior ^ o-dinitroaniline ÄthanolEthanol ÄthanolEthanol 40 bis 4140 to 41 N,N-Di-n-butyl-4-chlor-2,6-dinitroanilinN, N-di-n-butyl-4-chloro-2,6-dinitroaniline ÄthanolEthanol ÄthanolEthanol unterhalb
Raumtemperaturbelow
Room temperature N,N-Di-n-propyl-4-trifluormethyl-
2,6-dinitroanilinN, N-di-n-propyl-4-trifluoromethyl-
2,6-dinitroaniline ReaktionsteilnehmerRespondents HexanHexane 41 bis 4341 to 43 M,N-DialIyl-4-chlor-2,6-dinitroaniIinM, N-dialyl-4-chloro-2,6-dinitroaniIine ÄthanolEthanol

Die nachstehend aufgeführten Verbindungen sind weitere Beispiele für solche Verbindungen, die sich
für die erfindungsgemäße Verwendung eignen und
nacK obigem Verfahren hergestellt werden können:The compounds listed below are further examples of such compounds that can
suitable for the use according to the invention and
According to the above process, the following can be produced:

N,N-Di-n-buty!-4-fluor-2,6-dinitroanilin,
N-Äthyl-N-n-buty]-2,6-dinitroanilin,
N-Methyl-N-n-propyl-2,6-dinitro-p-toluidin,
N,N-Di-n-propyl-4-n-butyl-2,6-dinitroanilin,N, N-di-n-buty! -4-fluoro-2,6-dinitroaniline,
N-ethyl-Nn-buty] -2,6-dinitroaniline,
N-methyl-Nn-propyl-2,6-dinitro-p-toluidine,
N, N-di-n-propyl-4-n-butyl-2,6-dinitroaniline,

N,N-Di-n-piOpyl-4-t-butyl-2,6-dinitroanilin,
N-n-Propyl-N-n-butyl-4-n-propyl-N, N-di-n-piOpyl-4-t-butyl-2,6-dinitroaniline,
Nn-propyl-Nn-butyl-4-n-propyl-

2,6-dinitroanilin,
N-Äthyi-N-n-propyl-4-isopropyl-2,6-dinitroaniline,
N-Ethyi-Nn-propyl-4-isopropyl-

2,6-dinitroanilin.2,6-dinitroaniline.

Die erfindungsgemäß verwendeten Verbindungen sind selektive Herbizide, die keimende Gräser in Gegenwart vorhandener Gräser und der meisten breitblätlrigen Pflanzen abtöten können. Die Verbindungen sind besonders wirksam bei der Bekämpfung keimender Unkrautgräser.The compounds used according to the invention are selective herbicides that germinate grasses in Can kill the presence of existing grasses and most broad-leaved plants. The connections are particularly effective in combating germinating weed grasses.

Ein Vorzug dieser Wirkstoffe ist, daß zur Abtötung keimender Getreidegräser wesentlich höhere Mengen angewendet werden müssen als zur Zerstörung keimender Unkrautgräser. Als »Vorauflauf-Herbizide« können die 2,6-Dinitroanilin-Verbindungen der Erfindung zur Vernichtung oder starken Verminderung der Unkrautgräser, insbesondere Digitaria sanguinalis, Setaria viridis und Setaria lutescens verwendet werden, die sich auf vorhandenem Rasen angesiedelt haben, welcher erwünschte Gräser, wie Poa Sp., Zoysia, St.-Augustin-Gras, Straußgras, Festuca Sp. und Cynodon dactylon aufweist. Sie können zur Vernichtung keimender Gräser auf landwirtschaftlich genutzten Flächen verwendet werden, auf denen Sojabohnen, Baumwolle und Erdbeeren angebaut werden oder bereits wachsen. Sie können zur Vernichtung keimender Gräser in Blumenrabatten und verschiedenen anderen Stellen wie Sandstraßen, Wegen, Straßenbanketten verwendet werden. Die Verbindungen werden auf die jeweilige Fläche in Mengen von 0,112 bis 22,42 kg/ha aufgebracht. Mengen oberhalb 22,4 kg/ha der gleichen Verbindung sind im allgemeinen notwendig, die meisten breitblättrigen Pflanzen zu schädigen. Mengen bis zu 71,74 kg/ha oder mehr an N,N-Dialkyl-2,6-dinitroanilin zeigten nur geringe Wirkung auf ausgewachsene Rasengräser. Die Verbindungen können auf die zu behandelnden Flächen in Form von Sprays oder Körnchen oder auf Trägern, wie Vermiculit oder Torf in bekannter Weise aufgebracht werden.One advantage of these active ingredients is that they are much higher to kill germinating cereal grasses Quantities must be applied than to destroy germinating weed grasses. As "pre-emergence herbicides" can destroy or strengthen the 2,6-dinitroaniline compounds of the invention Reduction of weed grasses, especially Digitaria sanguinalis, Setaria viridis and Setaria lutescens are used that have settled on existing lawns, which grasses are desired, such as Poa Sp., Zoysia, St. Augustine grass, ostrich grass, Festuca Sp. and Cynodon dactylon. she can be used to destroy germinating grasses on agricultural land, on which soybeans, cotton and strawberries are grown or are already growing. You can for the destruction of germinating grasses in flower beds and various other places such as sand roads, Because of, street banquets are used. The connections are made on the respective surface applied in amounts of 0.112 to 22.42 kg / ha. Amounts above 22.4 kg / ha of the same compound are generally necessary to damage most broad-leaved plants. Amounts up to 71.74 kg / ha or more of N, N-dialkyl-2,6-dinitroaniline showed little effect on adults Lawn grasses. The compounds can be applied to the surfaces to be treated in the form of sprays or Granules or on supports such as vermiculite or peat in a known manner.

Unter den keimenden Gräsern, die mit den Verbindungen der Erfindung bekämpft werden können, befinden sich solche unerwünschten Gräser wie Digitaria sanguinalis, Digitaria ischaemum, Setaria viridis und Setaria lutescens, Sorghum halepense, Eleusine indica, Cenchrus pauciflorus, Panicum capillare u. dgl. sowie die Keimlinge erwünschter Gräser, wie Cynodon dactylon, Poa pratensis, Festuca Sp., Dactylis glomerata, Agrostis alba, Sorghum vulgäre u. dgl.Among the germinating grasses that can be controlled with the compounds of the invention, there are such unwanted grasses as Digitaria sanguinalis, Digitaria ischaemum, Setaria viridis and Setaria lutescens, Sorghum halepense, Eleusine indica, Cenchrus pauciflorus, Panicum capillare and the like. and the seedlings of desirable grasses, such as Cynodon dactylon, Poa pratensis, Festuca Sp., Dactylis glomerata, Agrostis alba, Sorghum vulgare and the like.

2,6-Dinitroanilin-Verbindungen mit zwei n-Propylgruppen am Aminostickstoffatom stellen eine bevorzugte Gruppe selektiver Herbizide der Erfindung dar auf Grund ihres breiten Sicherheitsspielraums zwischen der wirksamen Konzentration zur Bekämpfung keimender Gräser und der Konzentration, bei der Kulturpflanzen in beträchtlichem Ausmaß geschädigt werden. Beispielsweise ergab sich bei Gewächshausversuchen mit N5N - Di - propyl - 2,6 - dinitroanilin, N.N-Di-n-propyM-chlor^o-dinitroanilin, N5N-Din - propyl - 4 - trifluormethyl - 2,6 - dinitroanilin und N1N - Di - η - propyl - 2,6 - dinitro - ρ - toluidin deren Fähigkeit, keimende Gräser bei Anwendungsmengen von 0,224 bis 0,8968 kg/ha schwer zu schädigen, wenn man die herbizide Verbindung als Spray auf die Versuchsfläche aufbrachte. Bei ähnlichen Gewächshausversuchen zeigten die vorstehend genannten Verbindungen nur geringe oder gar keine Schädigung bei Nutzpflanzen, wie Sojabohnen und Baumwolle, entweder als Keimlinge oder als ausgewachsene Pflanzen in Mengen von 4,484 oder 8,968 kg/ha oder noch höher. Andere Nutzpflanzen, die bei Verwendung herbizid wirksamer Mengen einer der vorstehend genannten bevorzugten Verbindungen nur geringe Schädigung zeigen, sind die Gräser Hafer und Weizen und die breitblättrigen Pflanzen Alfalfa,2,6-Dinitroaniline compounds having two n-propyl groups on the amino nitrogen atom constitute a preferred group of selective herbicides of the invention because of their wide safety margin between the concentration effective for controlling germinating grasses and the concentration at which crops are significantly damaged. For example, greenhouse experiments with N 5 N - di - propyl - 2,6 - dinitroaniline, NN-di-n-propyM-chloro ^ o-dinitroaniline, N 5 N-din - propyl - 4 - trifluoromethyl - 2,6 - dinitroaniline and N 1 N - di - η - propyl - 2,6 - dinitro - ρ - toluidine whose ability to seriously damage germinating grasses at application rates of 0.224 to 0.8968 kg / ha when the herbicidal compound is sprayed onto the Test area applied. In similar greenhouse experiments, the abovementioned compounds showed little or no damage to useful plants, such as soybeans and cotton, either as seedlings or as adult plants in amounts of 4.484 or 8.968 kg / ha or even higher. Other useful plants which show only slight damage when using herbicidally effective amounts of one of the abovementioned preferred compounds are the grasses oats and wheat and the broad-leaved plants alfalfa,

ίο grüne Bohnen, Sojabohnen, Erdbeeren, Rettiche, Rosenpappel, Gurken, Baumwolle, Warzenmelonen u. dgl.ίο green beans, soybeans, strawberries, radishes, Rose poplar, cucumber, cotton, wart melons and the like.

Die mangelnde Giftigkeit der vorstehend genannten Verbindungen auf Rasenstücke ausgewachsener Gräser wurde beim Aufbringen von 71,74 kg/ha N,N-Di-n-prcpyl-2,6-dinitroanilin auf Rasen von Straußgras, Cynodon dactylon und St.-Augustin-Gras im Gewächshaus sichergestellt. Nach Beendigung dieses Versuches konnte, bei den ausgewachsenen Rasen keine wahrnehmbare Schädigung festgestellt werden. Feldversuche wurden unter Verwendung der gleichen Verbindung als selektives Herbizid zur Vernichtung keimender Gräser durchgeführt. Es wurden größere Mengen verwendet, da die herbizide Aktivität der Verbindung über einen Zeitraum von mehreren Wochen andauern sollte. Die Ergebnisse dieser Feldversuche unter Verwendung eines körnigen Präparates von N,N-Di-n-propyI-2,6-dinitroaniIin zur Vernichtung von Digitariasanguinalis-Keimlingen sind in Tabelle II angegeben. In der ersten Spalte ist die Anwendungsmenge der aktiven Verbindung in Kilogramm je Hektar und in Spalte 2 die prozentuale Vernichtung der Keimlinge im Vergleich zur Anzahl der Digitaria-sanguinalis-Pflanzen auf einer Kontrollfläche angegeben. The lack of toxicity of the above compounds on adult lawns Grasses became from when N, N-di-n-prcpyl-2,6-dinitroaniline was applied to lawns at 71.74 kg / ha Ostrich grass, Cynodon dactylon and St. Augustine grass were secured in the greenhouse. After completion of this test, no noticeable damage was found in the adult lawns will. Field trials were carried out using the same compound as the selective one Herbicide carried out to destroy germinating grasses. Larger amounts have been used since the herbicidal activity of the compound should continue for a period of several weeks. The results of these field trials using a granular preparation of N, N-di-n-propyI-2,6-dinitroaniIin for the destruction of digitariasanguinalis seedlings are given in Table II. The first column shows the application rate of the active compound in kilograms per hectare and in column 2 the percentage destruction of the seedlings compared to the number of Digitaria sanguinalis plants indicated on a control area.

Tabelle IITable II

Wirkung von N,N-Di-n-propyl-2,6-dinitroanilin bei der Vernichtung keimender Digitaria sanguinalis imEffect of N, N-di-n-propyl-2,6-dinitroaniline in destroying germinating Digitaria sanguinalis im

FeldversuchField trial

AnwendungsmengeApplication amount Vernichtungdestruction kg/hakg / ha /o/O 2,82.8 67 bis 99,967 to 99.9 50 5,650 5.6 87 bis 99,987 to 99.9 11,211.2 98,2 bis 10098.2 to 100 22,422.4 99,7 bis 10099.7 to 100 33,633.6 100100 55 44,855 44.8 99,9 bis 10099.9 to 100

Ein emulgierbares Präparat mit 1,812 kg Ν,Ν-Din-propyl-2,6-dinitroanilin je 3,8 1 Konzentrat ergab eine ähnliche Wirksamkeit bei der Vernichtung von Digitaria-sanguinalis-Keimlingen im Feldversuch.An emulsifiable preparation with 1.812 kg Ν, Ν-din-propyl-2,6-dinitroaniline 3.8 l each concentrate showed a similar effectiveness in the destruction of Digitaria sanguinalis seedlings in the field test.

Die Erfindung wird durch die folgenden Ver gleichsversuche weiter erläutert. Die Zahlen in der Tabelle geben den Schädigungsgrad nach der Aufbringung der herbiziden Verbindung in der angegebenen Menge wieder. 0 bedeutet keine Schädigung, während 4 eine maximale Schädigung, d. h. eine Abtötung der Pflanze, bedeutet.The invention is further illustrated by the following comparative tests. The numbers in the Table give the degree of damage after application of the herbicidal compound in the specified table Crowd again. 0 means no damage, while 4 means maximum damage, i.e. H. one Killing the plant, means.

Herbizidherbicide

MCP (4-Chlor-2-methylphenoxyessigsäure)MCP (4-chloro-2-methylphenoxyacetic acid)

DINOSEB (2-sek-ButyI-4,6-dinitrophenol)DINOSEB (2-sec-ButyI-4,6-dinitrophenol)

DNOC (2-MethyI-4,6 -dinitrophenol)DNOC (2-methyl-4,6-dinitrophenol)

2,4-D (2,4-Dichlorphenoxyessigsä ure2,4-D (2,4-dichlorophenoxyacetic acid

kg/hakg / ha

4,54.5

2,22.2

1.11.1

0,560.56

4,5 2,2 1,1 0,564.5 2.2 1.1 0.56

4,5 2,2 4.5 2.2

1,11.1

0,560.56

4,5 2,2 4.5 2.2

Tabelle III Table III

SchädigungsgradDegree of damage

I. bekannter HerbizideI. Known herbicides

Behandlung vor dem AuflaufenTreatment before emergence

Behandlung nach dem AuflaufenTreatment after emergence

« 2«2

l3 Ul3 U

' 2 1'2 1

1 J41 J4

11

0 j r,0 y r,

BB.

■%■%

h a h a

"33 g"33 g

8S8S

U ! οU! ο

: 0 i 0: 0 i 0

! o I o! o I o

CC.

, ° S c, ° S c

1
11
1

ο ! οο! ο

ο ! οο! ο

4
34th
3

-1
2
0-1
2
0

o ■o ■

4
4
3
34th
4th
3
3

4 3 34 3 3

3 0 0 03 0 0 0

0 00 0

4 4 4 44 4 4 4

ί Iί I

2 |32 | 3

4 j 1 14 j 1 1

II! -sII! -s

2. erfindungsgetnäßer Herbizide2. herbicides according to the invention

kg/fa»kg / fa » jj Behandlung vor dem Auflauf:::Treatment before emergence ::: C
I
si C.
I.
si ■S"
'Bi
S ■ S "
'Bi
S. Senfmustard II.
ifif
8585 SS.
Ii.Ii. 1
J
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J
O II. Behandlung nach dem AuflaufenTreatment after emergence jj ! Sojabohncfi! Soybean cfi atat
ii
■1■ 1
SS. < Senf < Mustard ifif
8585 FuchsschwanzFoxtail CrießwurzelCrießwurzel Herbizidherbicide 99 2,32.3 οο
11 11 44th 2,72.7 3,73.7 44th 0,80.8 1 Baumwolle 1 cotton ii 1,21.2 1.81.8 1,71.7 1,81.8 1,51.5 N,N-Di-n-propyl-N, N-di-n-propyl- 4,54.5 1.11.1 0.30.3 0,20.2 44th 1.91.9 3.93.9 44th 0,30.3 0.70.7 11 0,60.6 1,31.3 1.31.3 1,31.3 1.41.4 2,6-dinitroaniIin2,6-dinitroaniIine 2,22.2 0,40.4 0,10.1 00 3,83.8 1.01.0 3.23.2 3,83.8 0,30.3 0,30.3 0,10.1 1,61.6 1,01.0 0,90.9 1,31.3 1,11.1 00 OJOJ 00 3,03.0 0,20.2 2,92.9 3,23.2 00 0.10.1 0,20.2 1,51.5 0,20.2 0,80.8 0,70.7 0.90.9 00 00 00 2,82.8 00 2,02.0 2,72.7 0.20.2 0.670.67 00 00 00 2,02.0 00 1,21.2 2,22.2 0.450.45 00 CC. 00 !.0! .0 00 00 2.!2.! 0.220.22 00 00 00 0,20.2 00 00 0,60.6 99 33 00 3.33.3 44th 33 44th 44th 0.30.3 0 70 7 1 71 7 ί 0ί 0 0303 ! 7! 7th N,N-Di-n-propyI-4-trifluor-N, N-di-n-propyI-4-trifluoro- 4.54.5 2.82.8 UU 3.03.0 44th 2.82.8 44th 44th 0.30.3 0707 00 1.31.3 1,71.7 0,30.3 11 methyl-2,6-dinitroani!inmethyl-2,6-dinitroani! in 3.43.4 0,80.8 ■j■ j 44th 22 44th 44th —- 00 —- -—- —- 2.22.2 "5 -j"5 -j 00 0.20.2 AA. 1,81.8 44th 44th 0.50.5 00 1.51.5 OJOJ 00 0,50.5 IJIJ K9K9 t)t) 0,60.6 44th 1.11.1 44th 44th 0.50.5 0.90.9 22 0.60.6 0.30.3 3.83.8 1.31.3 44th 44th 0,560.56 00 0.30.3 00 3.53.5 00 44th 44th 0,450.45 0.70.7 00 0,30.3 3.83.8 0.80.8 44th 44th 0.22 ! 0.22 ! 0.3'0.3 ' 0.30.3 0.30.3 3.23.2 00 3.63.6 3.83.8 00

Fortsetzungcontinuation

kg/hakg / ha MaisCorn Behandlung vor dem AuflaufenTreatment before emergence SojabohnenSoybeans DigitariaDigitaria Senfmustard 11 NN GrießwurzelSemolina root MaisCorn 11 Behandlung nach dem AuflaufenTreatment after emergence SojabohnenSoybeans DigitariaDigitaria Senfmustard -- FuchsschwanFox swan GrieBwurzelSemolina root 8,98.9 11 0,50.5 44th GänsefuB
(ChenopodiuGoose foot
(Chenopodiu 11 22 0,50.5 44th GänsefuB
(ChenopodiuGoose foot
(Chenopodiu 33 22 Herbizidherbicide 4,54.5 1,51.5 Baumwollecotton 22 44th 3,53.5 33 22 Baumwollecotton 3,53.5 N,N-Di-n-pr opy 1-4-brom -N, N-Di-n-pr opy 1-4-bromine - 2,22.2 0,30.3 0,0, 11 3,33.3 3,53.5 33 1,31.3 0,50.5 2,6-dinitroanilin2,6-dinitroaniline 1,01.0 00 1,51.5 00 3,73.7 33 3,33.3 1,31.3 0,560.56 00 0,30.3 00 33 33 33 00 0,280.28 00 0,60.6 00 33 2,52.5 33 00 0,1350.135 00 00 00 22 11 33 00 .8,9.8.9 11 00 11 44th —- 00 22 4,54.5 22 00 22 44th 11 44th 44th N,N-Di-n-propyl-4-fluoro-N, N-di-n-propyl-4-fluoro- 2,22.2 11 22 22 44th 00 44th 33 2,6-dinitroaniIin2,6-dinitroaniIine 1,11.1 00 00 00 33 00 44th 33 00 99 —- 33 11 44th 33 44th 33 00 11 33 22 22 4,54.5 22 00 00 44th 33 44th 44th 00 11 33 33 22 00 HN-Di-n-propyM-chlor-HN-Di-n-propyM-chlor- 2,22.2 22 11 00 44th 22 33 44th 11 00 33 22 22 00 2,6-dinitroanilin2,6-dinitroaniline 1,11.1 00 00 00 3,83.8 0,80.8 44th 44th 00 22 0,90.9 00 00 00 3,83.8 00 2,82.8 44th 11 0,670.67 00 00 00 3,23.2 00 2,82.8 44th 0,560.56 00 00 00 33 00 2,22.2 3,83.8 0,450.45 00 00 00 2,82.8 00 11 33 0,220.22 00 00 00 1,51.5 00 1,81.8 3,33.3 1,31.3 99 2,32.3 00 2,72.7 44th 33 0,80.8 22 0,70.7 2,02.0 33 22 22 4,54.5 2,72.7 00 0,70.7 44th 2,72.7 44th 44th 0,30.3 2,02.0 2,72.7 22 2,72.7 22 N,N-Di-n-propyl-2,6-dinitro-N, N-di-n-propyl-2,6-dinitro- 2,22.2 11 0,30.3 00 44th 33 44th 44th 00 1,71.7 1,31.3 22 1,71.7 1,31.3 1,71.7 p-toluidinp-toluidine 1,11.1 0,50.5 00 00 3,93.9 1,31.3 44th 44th 1,31.3 00 1,51.5 22 11 11 0,90.9 0,30.3 00 00 3,93.9 0,70.7 3,93.9 44th 11 11 0,670.67 0,10.1 00 00 3,63.6 0,70.7 3,63.6 44th 00 0,450.45 00 00 00 3,63.6 0,10.1 3,73.7 3,93.9 0,220.22 00 00 00 2,82.8 0,20.2 3,13.1 3,93.9 2,32.3 99 11 00 0,70.7 44th 33 2,02.0 3,43.4 1,31.3 1,31.3 3,73.7 33 33 4,54.5 0,70.7 00 0,70.7 44th 1,31.3 3,73.7 44th 1 31 3 0,30.3 3,73.7 33 33 2,72.7 N,N-Diäthyl-N, N-diethyl 2,22.2 0,30.3 00 0,30.3 3,53.5 0,70.7 2,72.7 3,73.7 00 1,31.3 0404 2929 2 32 3 33 2,12.1 2,6-dinitroanilin2,6-dinitroaniline 1,11.1 00 00 0,30.3 11 00 2,52.5 3,33.3 11 0,70.7 00 1,31.3 11 3737 11 99 00 00 00 44th 33 00 11 00 0606 11 11 11 1,31.3 00 4,54.5 00 00 00 44th 00 44th 44th 00 11 00 00 00 00 N,N-Diäthyl-2,6-dinitro-N, N-diethyl-2,6-dinitro- 2,22.2 00 00 00 33 00 33 44th 00 00 4-chloranilin4-chloroaniline 1,11.1 00 00 00 22 00 11 33 11 00 99 33 00 11 44th 33 00 22 11 11 22 22 22 4,54.5 00 00 00 44th 33 44th 44th 00 11 22 11 22 22 N,N-Diäthyl-2,6-dinitro-N, N-diethyl-2,6-dinitro- 2,22.2 00 00 00 33 22 44th 44th 00 00 00 11 00 11 11 p-toluidinp-toluidine 1,11.1 00 00 00 3,33.3 11 44th 44th 00 00 11 11 11 11 0,90.9 00 00 00 3,53.5 0,50.5 2,72.7 33 00 22 0,670.67 00 00 00 3,53.5 0,50.5 33 33 00 0,450.45 00 00 00 33 0,50.5 1,51.5 2,52.5 0,220.22 00 00 00 11 00 0,50.5 22 00 00 0,50.5 00

2,62.6 rifluormrifluorm ZZ OO OO ONON Ji
f-t- Ji
ft- Z *Z * •• OJOJ OO OO ^-^ - 33 fluflu ZZ ^- ^ - IOIO ZZ OO OO OO , .,. IOIO rsrs ZZ OO OO OO I .I. toto ZZ OO toto ΠΝΠΝ ZZ OO OO OO ! .! . toto JiJi ZZ HerHer !5! 5 ίί S?S? -dinitro.-dinitro. ethyl-ethyl IOIO JiJi -dinitro.-dinitro. rifluormrifluorm 1S* 1 S * OO IOIO UlUl 5'5 ' υυ
SS.
3·3 · ^^^^ toto ZZ JiJi OnOn vOvO M-.M-. toto thyl-2,6-ethyl-2,6- ,N-, N- JiJi ONON VDVD IOIO ZZ IoIo -dinitro-dinitro ZZ JiJi ONON VOVO IOIO rifluormrifluorm ZZ bizidbicide trtr handlunact inilininilin CSCS hyl-N-nhyl-N-n IOIO UlUl inilininilin ethyl-ethyl hyl-N-nhyl-N-n toto ONON OO 1-2,6-dinitro-1-2,6-dinitro- ftft
3·3 ·
ZZ ,, Di-n-buDi-n-bu UlUl ^4 ^ 4 dinitroanilindinitroaniline Di-n-buDi-n-bu UiUi -J-J Di-n-buDi-n-bu OO inilininilin Di-n-buDi-n-bu UlUl -O.-O. ethylanilinethylaniline Diäthvl-Diethvl g vorg before ο οο ο vOvO -propyl--propyl- OO OO -butyl--butyl- IOIO OO OO toto n-butyl-4-tri-n-butyl-4-tri- OO OO tyl-4-chlor-tyl-4-chlorine- OO OO tyl-4-trifluor-tyl-4-trifluoro- OO OO tyl-2,6-dinitro-tyl-2,6-dinitro- OO S.S. OO OO OO ^^^^ ____ jiji 2,6-dinitro-2,6-dinitro- MaisCorn 8*8th* ,-,, -, Ji OnJi On ONON ^o^ o , .,. OO IOIO UiUi VDVD VOVO UlUl VDVD VDVD OO UiUi VOVO UiUi VOVO IOIO -J-J I .I. J^J ^ OO OO OO OO OO OO OO OO OJOJ OO OO OO OO OO OO Baumwollecotton CC. IOIO OO OO „" OO OO OO s1 s 1 OO OO OJOJ . .. . OO OO OO OO OO OO OO OO OO OO OJOJ OO OO OO OO OO toto SojabohnenSoybeans lfenlfen IOIO OJOJ IOIO OJOJ OO OO OJOJ OJOJ OO toto OJOJ OjOj JiJi OO IoIo OJOJ OJOJ JO
Ui JO
Ui IOIO OJOJ OO —- OO —- OJOJ OJOJ OO DigitariaDigitaria oO OO OO OO OO OO OO OO OO OO OO OO JiJi OO OO OO OO OO __ OO OJOJ OO OO OO OO OO OO OO Senfmustard J'J ' IoIo OO OO OO UlUl OJOJ OJOJ OO OO OJ OJOJ OJ ^*^ * . .. . IOIO OJOJ OJOJ OO , .,. OJOJ JiJi OO OO ,_, _ OO OO OO OO OO IoIo OjOj OO OO OO OO , .,. IOIO OO OJOJ yjyj
"—i"—I OO OO ,_*, _ * , .,. ^^^^ JiJi JiJi toto GänsefußGoosefoot IOIO O '-»JO '- »J j^.j ^. OO IOIO OO JiJi JiJi „" JiJi JiJi OJOJ OO JiJi UlUl toto JiJi (Chenopodium)(Chenopodium) BehaBeha —- , .,. OJOJ JiJi IOIO OJOJ UiUi IOIO toto OJOJ OO ·—- OJOJ IoIo OJOJ JiJi OJOJ ,—, - toto OJOJ IOIO OJOJ toto PP. OJOJ OJOJ toto —- ►—►— toto OJOJ JiJi OJOJ FuchsschwanzFoxtail I
' 3 I.
'3 IO OIO O IOIO '-»J'-' J IOIO OJOJ OJOJ UlUl -J-J -J-J OJOJ JiJi SS. OJ JiOJ Ji UlUl UiUi OO JiJi OO OJOJ OJOJ JiJi GrießwurzelSemolina root Q.Q. OJ O-OJ O- OJOJ OJOJ OO OO OJOJ OO —- 0,70.7 OO OJOJ UlUl OO OO JiJi MaisCorn toto UlUl j.j. OJOJ J,J, JiJi OO -J-J -J-J JiJi JiJi J- J*J- J * OO OO —- —- --j--j OO OO OO Baumwollecotton AuflEEd OO —- —- —- OO —- —- OO OO OO SojabohnenSoybeans lufeilufei OO —- —- IOIO OO toto toto -J-J OO —- OO DigitariaDigitaria ρρ IoIo OO UlUl OO OO toto IOIO IOIO OO I .I. toto , .,. I .I. OJOJ OO OO OO OO Senfmustard OO IoIo —- toto OJOJ IOIO toto IOIO OO OO —- —- IOIO -- —- IOIO IJIJ OJOJ toto OO OO toto Gänsefuß
(Chenopodium)Goosefoot
(Chenopodium) OO OO I ,I, IOIO UlUl OO ^_^ _ OO FuchsschwanzFoxtail OO IOIO JiJi IOIO „" r*r * UlUl OO Grieß wurzelSemolina root OO IOIO OO OJOJ ^^^^ IOIO toto —- OO JOJO ■a■ a OJOJ IOIO IoIo -dinitro.-dinitro. oluidinoluidine UiUi inilininilin UlUl UlUl OO OO OO OO OO OO OJOJ JiJi OO „" _^_ ^ JiJi OJOJ JiJi —- ^_^ _ —- —- —- IOIO —- IOIO IOIO toto —- toto OO toto

Fortsetzungcontinuation

kg/hakg / ha Mais
ICorn
I. Behandlung voiTreatment voi SojabohnenSoybeans DigitariaDigitaria r dem Auflaufenr accruing 11 NN GrießwurzelSemolina root MaisCorn Behandlung nach dem AuflaufenTreatment after emergence SojabohnenSoybeans DigitariaDigitaria Senfmustard BB. FuchsschwanFox swan υυ
SS. 99 0..0 .. 00 44th Gänsefuß
(ChenopodiuGoosefoot
(Chenopodiu FuchsschwanFox swan Gänsefuß
(ChenopodiuGoosefoot
(Chenopodiu Herbizidherbicide ~> ■>~> ■> 00 Baumwollecotton 00 33 Senfmustard 3,53.5 44th Baumwollecotton N-Äthyl-N-n-propyl-N-ethyl-N-n-propyl- 99 00 00 00 44th ·>·> 33 44th 00 22 22 ->-> ΊΊ 2.6-dinitroanilin2,6-dinitroaniline ~> Ί~> Ί 00 00 00 33 11 44th 44th 33 N-n-Butyl-N-n-propyl-N-n-butyl-N-n-propyl- 4,54.5 00 00 11 44th 22 22 33 0,50.5 11 11 3,53.5 2,52.5 Ί ^ Ί ^ 2,6-dinitroanilin2,6-dinitroaniline 2,22.2 00 00 0,50.5 1,51.5 00 33 44th 00 00 22 11 3.53.5 11 N-Methyl-N-n-propyl-N-methyl-N-n-propyl- 1,11.1 00 33 22 11 τ «jτ «j 11 33 2,6-dinitroanilin2,6-dinitroaniline 0,90.9 00 33 11 33 33 11 N-Äthyl-N-n-propyl-N-ethyl-N-n-propyl- 0,670.67 33 22 33 33 2,6-dinitro-p-toluidin2,6-dinitro-p-toluidine 0,450.45 33 00 -)-) 33 0,220.22 ->-> 00 33 ·>·> 1.11.1 33 00 11 00 0,90.9 33 00 33 33 N-Äthyl-N-n-butyl-N-ethyl-N-n-butyl- 0.670.67 33 00 22 33 2,6-dinitro-p-toluidin2,6-dinitro-p-toluidine 0,450.45 33 00 22 33 0,220.22 22 00 11 77th 99 11 00 44th 00 00 22 00 00 11 00 00 4,54.5 00 00 44th 00 33 44th 00 N-Allyl-N-methyl-4-trifluor-N-allyl-N-methyl-4-trifluoro- 2,22.2 ΌΌ 00 00 33 22 22 44th 00 methyl-2,6-dinitroanilinmethyl-2,6-dinitroaniline 99 00 00 11 44th 00 11 33 00 00 11 00 00 4,54.5 0.50.5 00 00 44th 00 44th 44th 00 N-Allyl-N-äthyl-4-trifluor-N-allyl-N-ethyl-4-trifluoro- 2,22.2 0,50.5 00 00 44th 33 44th 44th 00 methyl-2,6-dinitroanilinmethyl-2,6-dinitroaniline 1,11.1 00 00 00 3,73.7 22 33 44th 0,90.9 —- 00 —- 44th 22 2,72.7 3,33.3 0,670.67 —- 00 —- 33 0,30.3 44th 44th 0,560.56 00 —- 00 33 II. 22 33 0,450.45 —- —- —- 33 11 22 33 0,220.22 00 00 00 11 00 22 33 1,11.1 —- 33 11 0,50.5 ττ 0,90.9 00 33 00 22 33 N-Allyl-N-äthyl-N-allyl-N-ethyl- 0,670.67 33 00 33 33 2,6-dinitro-p-toluidin2,6-dinitro-p-toluidine 0,450.45 22 00 22 33 0,220.22 22 00 11 22 99 0,20.2 0,20.2 3,83.8 00 00 11 —- —- —- —- —- 4,54.5 00 00 3,83.8 00 3,43.4 3,83.8 11 11 33 11 —- 22 N,N-Di-allyl-N, N-di-allyl- 2,22.2 00 0,40.4 00 2,32.3 2,82.8 2,82.8 3,53.5 11 —- 11 1,51.5 11 22 11 2,6-dinitroanilin2,6-dinitroaniline 1,11.1 00 00 00 2,52.5 2,52.5 0,80.8 3,33.3 00 11 00 11 00 22 11 99 33 00 00 44th 0,30.3 00 33 00 11 00 11 11 11 11 4,54.5 22 00 00 44th 00 44th 44th 00 00 N,N-Di-allyl-4-trifluor-N, N-di-allyl-4-trifluoro- 2,22.2 11 00 00 44th 22 44th 44th 00 methyl-2,6-dinitroanilinmethyl-2,6-dinitroaniline UU 0,30.3 00 00 3,53.5 11 44th 44th 0,90.9 00 00 00 3,73.7 11 3,33.3 3,53.5 0,670.67 00 00 00 3,33.3 0,30.3 2,72.7 3,33.3 0,450.45 00 00 00 2,72.7 00 2,32.3 33 0,220.22 00 00 00 22 0,30.3 2,32.3 2,72.7 00 00 1,31.3 2,32.3 00 00

Fortsetzungcontinuation

kg/hakg / ha MaisCorn Behandlung vor dem AuflaufenTreatment before emergence SS. DigitariaDigitaria Senfmustard 11 NN 88th 11 MaisCorn 11 Behandlung nach dem AuflaufenTreatment after emergence CC.
υυ DigitariaDigitaria Senfmustard 11 II. GrießwuiGrießwui 1,11.1 SojabohnSoybean 33 00 '•i'• i II. GrießwurSemolina sausage 22 SojabohnSoybean idiuidiu Fuchssch·Fuchssch · Herbizidherbicide 0,90.9 33 00 Gänsefuß
(ChenopcGoosefoot
(Chenopc Fuchssch·Fuchssch · 2,52.5 υυ Gänsefuß
(ChenopcGoosefoot
(Chenopc 0,670.67 BaumwolCotton 33 00 00 33 1,71.7 BaumwolCotton N,N-Di-allyl-4-methyl-N, N-di-allyl-4-methyl- 0,450.45 33 00 22 33 22 00 2,6-dinitroanilin2,6-dinitroaniline 8,98.9 22 44th 11 11 33 1,31.3 00 11 22 4.54.5 11 00 44th 11 11 22 1,31.3 00 00 11 2,22.2 00 00 44th 11 44th 3,53.5 22 00 00 N-(4-Trifluoromethyl-N- (4-trifluoromethyl- 1,11.1 00 0.50.5 00 33 00 44th 44th 22 0,50.5 00 2,6-dinitrophenyl)-2,6-dinitrophenyl) - 8,98.9 00 00 00 44th 11 44th 44th 11 11 22 1,51.5 pyrrolidinpyrrolidine 4,54.5 00 00 00 33 11 00 33 00 11 11 11 11 22 2,22.2 00 00 00 33 00 11 44th 00 00 00 00 11 11 11 N-(4-Chlor-2,6-dinitro-N- (4-chloro-2,6-dinitro- 1,11.1 00 00 00 22 00 11 44th 00 00 00 00 00 11 22 00 phenyl)-pyrrolidinphenyl) pyrrolidine 8,98.9 0,50.5 00 00 44th 2,52.5 00 33 00 00 22 22 11 00 4,54.5 00 00 00 44th 00 00 11 00 11 22 22 11 2,52.5 2,22.2 00 00 00 33 00 3,53.5 44th 00 00 22 00 22 22 N-(4-Methyl-2,6-dinitro-N- (4-methyl-2,6-dinitro- 1,11.1 00 00 00 33 00 22 44th 00 0,50.5 00 11 00 22 2*2 * phenyl)-pyrrolidinphenyl) pyrrolidine 8,98.9 00 00 00 44th 11 11 33 00 00 11 11 22 00 4,54.5 00 00 00 44th 11 11 33 00 00 00 00 2,22.2 00 00 00 33 11 44th 44th 00 00 N-(4-Trifluoromethyl-N- (4-trifluoromethyl- 1,11.1 00 00 00 33 00 44th 44th 00 2,6-dinitrophenyl)-2,6-dinitrophenyl) - 8,98.9 11 00 00 44th 33 33 22 00 piperidinpiperidine 4,54.5 33 00 22 44th 33 33 22 11 2,22.2 11 00 22 3,53.5 44th 44th 00 22 4-(t-Butyl)-2,6-dinitro-4- (t-butyl) -2,6-dinitro- 1,11.1 00 22 11 3,73.7 44th 33 11 N,N-di-(n-propyl)-anilinN, N-di (n-propyl) aniline 0,560.56 00 11 00 33 44th 33 0,280.28 o"O" 00 00 3,33.3 3,73.7 2,72.7 0,1350.135 00 00 00 33 2,32.3 33 8,98.9 22 00 00 44th 3,33.3 3,33.3 11 00 4,54.5 00 00 00 44th 2,72.7 33 11 11 2,22.2 00 00 00 3,53.5 44th 33 22 4-(sek- Butyl)-2,6-dinitro-4- (sec- butyl) -2,6-dinitro- 1.11.1 00 00 00 33 44th 33 00 N,N-di-(n-propyl)-anilinN, N-di (n-propyl) aniline 0,550.55 00 00 00 33 3,53.5 33 0,280.28 00 00 00 22 3,33.3 1,51.5 00 00 22 33 00 11 22 00

Diese Versuchsergebnisse zeigen, daß die erfindungsgemäßen Mittel im Gegensatz zu den bekannten Mitteln, insbesondere auch in bereits aufgelaufenen Kulturen, gegen keimende Unkräuter eingesetzt werden können.These test results show that the agents according to the invention in contrast to the known Means, in particular also in crops that have already emerged, can be used against germinating weeds can.

Claims (1)

Patentanspruch:Claim: Verwendung von Dinitroanilinderivaten der allgemeinen FormelUse of dinitroaniline derivatives of the general formula 15 Κ»15 Κ » worin R für eine n-AIkyigruppe mit 2 bis 4 KoIi- 4 KühlenstolTatonien ist. oder R und R /u-where R is for an n-alkyl group with 2 to 4 KoIi- 4 KühlenstolTatonien. or R and R / u- lenstoffatomen oder die Allylgruppe steht. R samrnen mit dem Stickstoffatom, mit welchemlenstoffatomen or the allyl group. R together with the nitrogen atom with which eine n-AIkylgruppe mit I bis 4 Kohlenstoffato- sie verknüpft sind, einen Piperidino- oder Pyrro-an n-alkyl group with I to 4 carbon atoms they are linked, a piperidino or pyrro men oder die Allylgruppe bedeutet und R lidinorcst bilden, wenn R" eine andere Bedeutunumen or the allyl group and form Ridinorcst when R "has another meaning Wasserstoff oder ein Halogenatom, die Trifluor- 5 als Wasserstoff besitzt, als selektive Vorauflauf-Hydrogen or a halogen atom, which has trifluoro 5 as hydrogen, as a selective pre-emergence methylgruppe oder eine Alkylgruppe mit 1 bis herbizide.methyl group or an alkyl group with 1 to herbicidal.
DEE21584A 1960-08-31 1961-08-24 Use of dinitroaniline derivatives as selective pre-emergence herbicides Pending DE1300727B (en)

Applications Claiming Priority (1)

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US5306660A 1960-08-31 1960-08-31

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DE (1) DE1300727B (en)
GB (1) GB917253A (en)
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Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3227734A (en) * 1964-11-13 1966-01-04 Shell Oil Co Herbicidal 4-methylsulfonyl-2,6-dinitro-n,n-substituted anilines
DE2013510C3 (en) * 1969-04-01 1985-11-14 United States Borax & Chemical Corp., Los Angeles, Calif. Use of 6-trifluoromethyl-2,4-dinitro-1,3-phenylenediamines as herbicides
FR2085214B1 (en) * 1970-02-10 1973-10-19 Baut Jacques
WO2023222836A1 (en) 2022-05-20 2023-11-23 Syngenta Crop Protection Ag Herbicidal compositions
WO2024023035A1 (en) 2022-07-25 2024-02-01 Syngenta Crop Protection Ag Herbicidal compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
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